Theoretical Study of Stereoselectivity for Syn-Selective Cross-Aldol Reactions of Aldehydes Catalyzed by Chiral Diamine Organocatalysts

Abstract:

Quantum mechanical calculations have been performed to study the stereoselectivities in the direct cross-aldol reactions of aldehydes catalyzed by simple chiral diamines. The detailed computational studies on the stereochemistry-controlling step of the subject reactions have been presented by DFT calculations at the B3LYP/6-31G* level. The poor agreement between the calculated and the observed diastereomeric ratio and enantiomeric excess values is obtained for all diamines catalysts. Further M06-2X calculations can provide a reasonable explanation for the observed syn-selectivities of the asymmetric cross-aldol reaction between propionaldehyde and 4-nitrobenzaldehyde.

• Periodical: Advanced Materials Research (Volumes 798-799)
• Pages: 59-62
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.798-799.59
• Online since: September 2013
• Authors: Cheng Yan Zhao, Ai Ping Fu, Hong Liang Li, Ping Wang, Yong Xu, Yun Bo Duan
• Keywords: DFT, Diamine, Organocatalysis, Stereoselectivity, Syn-Aldol

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